• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】27141

【品名】methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3,3-dimethylbutanoate

【CA登记号】

【 分 子 式 】C12H23NO4

【 分 子 量 】245.31896

【元素组成】C 58.75% H 9.45% N 5.71% O 26.09%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(II)

The esterification of N-(tert-butoxycarbonyl)-L-tert-butylglycine (I) with DBU and methyl iodide gives the corresponding methyl ester (II), which is condensed with dimethyl methylphosphonate by means of butyllithium in THF yielding N-(tert-butoxycarbonyl)-L-tert-butylglycylmethylphosphonic acid dimethyl ester (III). The reaction of benzyl glyoxylate (IV) (obtained by IO4H oxidation of dibenzyl L-tartrate (V)) with phosphonic ester (III) by means of triethylamine in acetonitrile affords 5(S)-(tert-butoxycarbonylamino)-6,6-dimethyl-4-oxo-2-heptenoic acid benzyl ester (VI). The condensation of (VI) with allyl 2-pivaloylacetate (VII)(obtained by reaction of pivaloyl chloride (VIII) with allyl acetate (A) by means of LHDMS in THF) by means of NaH in THF provides the intermediate (IX). Selective elimination of the allyloxycarbonyl group of (IX) by means of Pd(PPh3)4 and pyrrolidine in dichloromethane/acetonitrile gives 5(S)-(tert-butoxycarbonylamino)-6,6-dimethyl-4-oxo-2(R)-(pivaloylmethyl)heptanoic acid benzyl ester (X). Hydrogenolysis of the benzyl ester group of (X) with H2 over Pd/C in ethanol gives the heptanoic acid (XI), which is condensed with the amino group of the cyclopentanecarboxylic ester (XII) by means of TBTU and NMM in dichloromethane to afford the corresponding amide (XIII).

1 Gauthier, J.-A.; Moss, N. (Bio-Mega, Inc.; Boehringer Ingelheim GmbH); Herpes ribonucleotide reductase inhibitors. EP 0837845; JP 1999508246; US 5672586; WO 9700855 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 27147 allyl acetate 591-87-7 C5H8O2 详情 详情
(I) 22251 (2S)-2-[(tert-butoxycarbonyl)amino]-3,3-dimethylbutyric acid;2-((tert-butoxycarbonyl)amino)-3,3-dimethylbutanoic acid;N-(tert-butoxycarbonyl)-3-methyl-L-valine 62965-35-9 C11H21NO4 详情 详情
(II) 27141 methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3,3-dimethylbutanoate C12H23NO4 详情 详情
(III) 27142 dimethyl (3S)-3-[(tert-butoxycarbonyl)amino]-4,4-dimethyl-2-oxopentylphosphonate C14H28NO6P 详情 详情
(IV) 27143 benzyl 2-oxoacetate C9H8O3 详情 详情
(V) 27144 dibenzyl 2,3-dihydroxysuccinate C18H18O6 详情 详情
(VI) 27145 benzyl (E,5S)-5-[(tert-butoxycarbonyl)amino]-6,6-dimethyl-4-oxo-2-heptenoate C21H29NO5 详情 详情
(VII) 27146 allyl 4,4-dimethyl-3-oxopentanoate C10H16O3 详情 详情
(VIII) 13597 2,2-Dimethylpropanoyl chloride; Pivaloyl chloride 3282-30-2 C5H9ClO 详情 详情
(IX) 27148 4-allyl 1-benzyl (2S,3S)-2-[(3S)-3-[(tert-butoxycarbonyl)amino]-4,4-dimethyl-2-oxopentyl]-3-(2,2-dimethylpropanoyl)butanedioate C31H45NO8 详情 详情
(X) 27149 benzyl (2R,5S)-5-[(tert-butoxycarbonyl)amino]-2-(3,3-dimethyl-2-oxobutyl)-6,6-dimethyl-4-oxoheptanoate C27H41NO6 详情 详情
(XI) 27150 (2R,5S)-5-[(tert-butoxycarbonyl)amino]-2-(3,3-dimethyl-2-oxobutyl)-6,6-dimethyl-4-oxoheptanoic acid C20H35NO6 详情 详情
(XII) 27151 benzyl 1-((1S)-1-amino-2-[[(1R)-1-ethyl-2,2-dimethylpropyl]amino]-2-oxoethyl)cyclopentanecarboxylate C22H34N2O3 详情 详情
(XIII) 27152 benzyl 1-((1S)-1-[[(2R,5S)-5-[(tert-butoxycarbonyl)amino]-2-(3,3-dimethyl-2-oxobutyl)-6,6-dimethyl-4-oxoheptanoyl]amino]-2-[[(1R)-1-ethyl-2,2-dimethylpropyl]amino]-2-oxoethyl)cyclopentanecarboxylate C42H67N3O8 详情 详情
Extended Information